Cesium carbonate → HCID 23000159, compound

HRID 398371Notes

Reaction equation

HRID 398371 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:21])[NH:11][C:12]([CH3:20])=[CH:13][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:21])[N:11]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:12]([CH3:20])=[CH:13][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 12089327HCID 12089327, compound

Product 1

HCID 23000159HCID 23000159, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

To a stirred solution of 3-benzyloxy-4-ethoxycarbonyl-6-methyl-2-pyridinone from step 1 above (17 g, 59 mmol) and tert-butyl bromoacetate (8.1 g, 59 mmol) in DMF (350 mL) at 0° C. was added cesium carbonate (19.3 g, 59 mmol). The mixture was stirred at 4° C. for 96 h. The salts were removed by filtration and the filtrate solvent was removed in vacuo. The residue was purified by flash column chromatography using 1:4 EtOAc:hexanes as eluant to give the title compound as an oil (9.5 g; HPLC RT=23.58, method B).

Workup

  1. customThe salts were removed by filtration
  2. customthe filtrate solvent was removed in vacuo
  3. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-b2af6d3a9c274d16aba52fd1127d6845
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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